The heiress to the Topshop fortune, 27, could be seen with a baby bump beneath her form-fitting black shirt while she spent time on her father Sir Philip Green's yacht in Monaco.
Meeks, 34, was also aboard the yacht, and at one point the controversial couple could be seen with their arms draped around one another.
Not only were Meeks and Chloe on board, but also were Chloe's parents (Sir Philip, 66, Lady Tina), Kris Jenner, 62, Corey Gamble, 34, Tommy Hilfiger, 67, and Formula 1's Lewis Hamilton.
The 33-year-old Hamilton is the new menswear ambassador for Hilfiger and is set to be unveiling his first collaborative collection with the brand.
The eclectic group could be seen eating in a communal seating area with luxurious furniture.
The outing comes almost two months after reports surfaced of Green's pregnancy with boyfriend Meeks. The couple began dating in June 2017 while the convict-turned-model was still married to Melissa Meeks. Scandal broke in the wake of the relationship going public, as Melissa was blindsided by the news.
"The first I learned of it was when I woke up and checked my phone," Melissa told the Daily Mail. "Some random person I don't know sent a direct message with the photograph of my husband kissing that woman. I went into shock. I felt nauseated. It was like a bomb had gone off and my whole world had been blown apart. I'd never heard of Chloe Green. I thought Jeremy was working."
Meeks somewhat contests that account, saying that his nine-year marriage was virtually done when he met Green.
"The people who really know me and my family know that my marriage had been over for a long time when I met Chloe," he told The Sunday Mirror in November. "For a while my wife and I had a very good life together and then for a long time we didn't. The marriage was over for a lot longer than people think."
After social media spats and media squabbles, Meeks, who has a son with Melissa, ultimately filed for divorce in October.
Engagement rumors from Meeks and Green have been rampant in recent months as Green was spotted sporting a large diamond ring in December.
In an interview with FV Magazine, Meeks did not address those rumors. Instead, he mused about being in love and emotionally fit.
"Love means everything, everything to me. It's what keeps people alive, it's what keeps people going, to love and to be loved," Meeks said. "I've never been in this place mentally, emotionally, physically, that I'm in right now. I've never been in such an amazing place."0comments
Meeks gained national attention when his attractive mugshot went viral in 2014. At the time, he was serving a 27-month sentence for grand theft and being a felon in possession of a firearm. He had previously been convicted of robbery and corporal injury to a child in 2002. Meeks was also a member of the North Side Gangster Crips gang.
After he was released from prison, he quickly signed a modeling contract and started walking runways around the world.